TW457234B - β-hydroxylactone derivatives of camptothecin, preparation processes, and anti-tumor pharmaceutical composition thereof - Google Patents

Info

Publication number

TW457234B

TW457234B TW085109645A TW85109645A TW457234B TW 457234 B TW457234 B TW 457234B TW 085109645 A TW085109645 A TW 085109645A TW 85109645 A TW85109645 A TW 85109645A TW 457234 B TW457234 B TW 457234B

Authority

TW

Taiwan

Prior art keywords

ethyl

hydroxy

compound

rmn

dmso

Prior art date

1995-06-21

Links

• Espacenet
• Global Dossier
• Discuss

• VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical class C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 title claims abstract description 22
• 230000000259 anti-tumor effect Effects 0.000 title claims abstract description 10
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 9
• 238000002360 preparation method Methods 0.000 title claims description 12
• 150000001875 compounds Chemical class 0.000 claims abstract description 178
• 238000000034 method Methods 0.000 claims abstract description 80
• -1 hydroxy lactone Chemical class 0.000 claims abstract description 60
• 230000008569 process Effects 0.000 claims abstract description 36
• VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 claims abstract description 22
• 150000003839 salts Chemical class 0.000 claims abstract description 22
• KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 claims abstract description 20
• 229940127093 camptothecin Drugs 0.000 claims abstract description 20
• 101710183280 Topoisomerase Proteins 0.000 claims abstract description 7
• 230000005764 inhibitory process Effects 0.000 claims abstract description 6
• 150000002596 lactones Chemical class 0.000 claims abstract description 4
• 150000001261 hydroxy acids Chemical class 0.000 claims abstract 2
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 252
• 125000000217 alkyl group Chemical group 0.000 claims description 116
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 100
• 239000007787 solid Substances 0.000 claims description 82
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 64
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 56
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 56
• 239000000047 product Substances 0.000 claims description 47
• 230000002829 reductive effect Effects 0.000 claims description 47
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 45
• 238000011049 filling Methods 0.000 claims description 40
• 239000000243 solution Substances 0.000 claims description 40
• 239000000203 mixture Substances 0.000 claims description 38
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 36
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 36
• 238000010992 reflux Methods 0.000 claims description 32
• 239000000725 suspension Substances 0.000 claims description 32
• 238000006243 chemical reaction Methods 0.000 claims description 30
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 26
• 238000011282 treatment Methods 0.000 claims description 26
• 235000002639 sodium chloride Nutrition 0.000 claims description 25
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 24
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 24
• 239000002904 solvent Substances 0.000 claims description 24
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 23
• 239000007789 gas Substances 0.000 claims description 22
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 21
• 239000011541 reaction mixture Substances 0.000 claims description 21
• 230000000875 corresponding effect Effects 0.000 claims description 19
• 239000002244 precipitate Substances 0.000 claims description 17
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 16
• 239000002253 acid Substances 0.000 claims description 15
• 238000004440 column chromatography Methods 0.000 claims description 14
• 229910052736 halogen Inorganic materials 0.000 claims description 14
• 150000002367 halogens Chemical group 0.000 claims description 14
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 13
• 229910052786 argon Inorganic materials 0.000 claims description 13
• 230000002079 cooperative effect Effects 0.000 claims description 13
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 13
• 239000000126 substance Substances 0.000 claims description 13
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 12
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 12
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 12
• 229910052938 sodium sulfate Inorganic materials 0.000 claims description 12
• 235000011152 sodium sulphate Nutrition 0.000 claims description 12
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
• 150000001412 amines Chemical class 0.000 claims description 11
• 239000003814 drug Substances 0.000 claims description 11
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 11
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
• 125000004432 carbon atom Chemical group C* 0.000 claims description 10
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
• 101150041968 CDC13 gene Proteins 0.000 claims description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 claims description 9
• 239000001257 hydrogen Substances 0.000 claims description 9
• 229910052739 hydrogen Inorganic materials 0.000 claims description 9
• 229910052740 iodine Inorganic materials 0.000 claims description 9
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 8
• 239000012267 brine Substances 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 238000010438 heat treatment Methods 0.000 claims description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 229910052757 nitrogen Inorganic materials 0.000 claims description 8
• 235000015170 shellfish Nutrition 0.000 claims description 8
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 8
• 229910052725 zinc Inorganic materials 0.000 claims description 8
• 239000011701 zinc Substances 0.000 claims description 8
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 7
• 239000000284 extract Substances 0.000 claims description 7
• 238000010898 silica gel chromatography Methods 0.000 claims description 7
• 238000003756 stirring Methods 0.000 claims description 7
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
• 238000001914 filtration Methods 0.000 claims description 6
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 6
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 6
• 239000011630 iodine Substances 0.000 claims description 6
• 238000007639 printing Methods 0.000 claims description 6
• JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 claims description 6
• 239000000052 vinegar Substances 0.000 claims description 6
• 235000021419 vinegar Nutrition 0.000 claims description 6
• VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 claims description 5
• 240000002853 Nelumbo nucifera Species 0.000 claims description 5
• 235000006508 Nelumbo nucifera Nutrition 0.000 claims description 5
• 239000007864 aqueous solution Substances 0.000 claims description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 239000003795 chemical substances by application Substances 0.000 claims description 5
• 238000001816 cooling Methods 0.000 claims description 5
• 238000005516 engineering process Methods 0.000 claims description 5
• 229910052731 fluorine Chemical group 0.000 claims description 5
• 239000011737 fluorine Chemical group 0.000 claims description 5
• 229910052700 potassium Inorganic materials 0.000 claims description 5
• 235000019260 propionic acid Nutrition 0.000 claims description 5
• 150000003254 radicals Chemical class 0.000 claims description 5
• 239000012279 sodium borohydride Substances 0.000 claims description 5
• 229910000033 sodium borohydride Inorganic materials 0.000 claims description 5
• 239000013589 supplement Substances 0.000 claims description 5
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
• 241000361919 Metaphire sieboldi Species 0.000 claims description 4
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
• 239000000460 chlorine Substances 0.000 claims description 4
• IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 4
• 238000000605 extraction Methods 0.000 claims description 4
• 239000000706 filtrate Substances 0.000 claims description 4
• 239000005457 ice water Substances 0.000 claims description 4
• 125000002757 morpholinyl group Chemical group 0.000 claims description 4
• 239000011591 potassium Substances 0.000 claims description 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
• 229920006395 saturated elastomer Polymers 0.000 claims description 4
• 239000012047 saturated solution Substances 0.000 claims description 4
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 3
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
• 241000759905 Camptotheca acuminata Species 0.000 claims description 3
• 244000082204 Phyllostachys viridis Species 0.000 claims description 3
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 3
• 125000004429 atom Chemical group 0.000 claims description 3
• 239000003153 chemical reaction reagent Substances 0.000 claims description 3
• 238000001035 drying Methods 0.000 claims description 3
• FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 3
• 150000004820 halides Chemical class 0.000 claims description 3
• 150000007857 hydrazones Chemical class 0.000 claims description 3
• 150000002431 hydrogen Chemical class 0.000 claims description 3
• 239000001301 oxygen Substances 0.000 claims description 3
• 229910052760 oxygen Inorganic materials 0.000 claims description 3
• 238000012856 packing Methods 0.000 claims description 3
• DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims description 3
• 239000011780 sodium chloride Substances 0.000 claims description 3
• 241000894007 species Species 0.000 claims description 3
• 239000000758 substrate Substances 0.000 claims description 3
• VSRBKQFNFZQRBM-UHFFFAOYSA-N tuaminoheptane Chemical compound CCCCCC(C)N VSRBKQFNFZQRBM-UHFFFAOYSA-N 0.000 claims description 3
• 229960003986 tuaminoheptane Drugs 0.000 claims description 3
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
• BDYRVZMWIBIACG-UHFFFAOYSA-N 2-bromoethyl 2-bromoacetate Chemical compound BrCCOC(=O)CBr BDYRVZMWIBIACG-UHFFFAOYSA-N 0.000 claims description 2
• QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 claims description 2
• MYQKIWCVEPUPIL-QFIPXVFZSA-N 7-ethylcamptothecin Chemical compound C1=CC=C2C(CC)=C(CN3C(C4=C([C@@](C(=O)OC4)(O)CC)C=C33)=O)C3=NC2=C1 MYQKIWCVEPUPIL-QFIPXVFZSA-N 0.000 claims description 2
• OQKYEMHWZYHWBL-UHFFFAOYSA-N 9h-fluoren-1-ylmethanol Chemical compound C1C2=CC=CC=C2C2=C1C(CO)=CC=C2 OQKYEMHWZYHWBL-UHFFFAOYSA-N 0.000 claims description 2
• 229910004298 SiO 2 Inorganic materials 0.000 claims description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
• HSJKGGMUJITCBW-UHFFFAOYSA-N beta-hydroxybutyraldehyde Natural products CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 claims description 2
• 239000004305 biphenyl Substances 0.000 claims description 2
• NMEGSGKCIWQRDB-UHFFFAOYSA-N butyl 2-bromoacetate Chemical compound CCCCOC(=O)CBr NMEGSGKCIWQRDB-UHFFFAOYSA-N 0.000 claims description 2
• 210000000078 claw Anatomy 0.000 claims description 2
• 229910052802 copper Inorganic materials 0.000 claims description 2
• 239000010949 copper Substances 0.000 claims description 2
• PKALZYQCBVPXNU-UHFFFAOYSA-N didiazomethane Chemical compound [N-]=[N+]=C=[N+]=[N-] PKALZYQCBVPXNU-UHFFFAOYSA-N 0.000 claims description 2
• PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 claims description 2
• 125000004494 ethyl ester group Chemical group 0.000 claims description 2
• 125000000524 functional group Chemical group 0.000 claims description 2
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
• 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 2
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical class II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
• 229910052742 iron Inorganic materials 0.000 claims description 2
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
• 229940017219 methyl propionate Drugs 0.000 claims description 2
• 150000004682 monohydrates Chemical class 0.000 claims description 2
• KWBLOUILYMNQAU-UHFFFAOYSA-N n-chloro-1-(3-fluorophenyl)methanamine Chemical compound FC1=CC=CC(CNCl)=C1 KWBLOUILYMNQAU-UHFFFAOYSA-N 0.000 claims description 2
• 238000010422 painting Methods 0.000 claims description 2
• 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
• QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
• 239000012264 purified product Substances 0.000 claims description 2
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
• 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims description 2
• 210000002784 stomach Anatomy 0.000 claims description 2
• 238000012546 transfer Methods 0.000 claims description 2
• 229910052721 tungsten Inorganic materials 0.000 claims description 2
• 239000003981 vehicle Substances 0.000 claims description 2
• 229910052770 Uranium Inorganic materials 0.000 claims 4
• RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims 4
• RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims 3
• 235000005206 Hibiscus Nutrition 0.000 claims 2
• 235000007185 Hibiscus lunariifolius Nutrition 0.000 claims 2
• 244000284380 Hibiscus rosa sinensis Species 0.000 claims 2
• 239000008186 active pharmaceutical agent Substances 0.000 claims 2
• NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical group ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims 2
• 125000004663 dialkyl amino group Chemical group 0.000 claims 2
• 241001233061 earthworms Species 0.000 claims 2
• MMZYCBHLNZVROM-UHFFFAOYSA-N 1-fluoro-2-methylbenzene Chemical compound CC1=CC=CC=C1F MMZYCBHLNZVROM-UHFFFAOYSA-N 0.000 claims 1
• 241000759909 Camptotheca Species 0.000 claims 1
• 102000019034 Chemokines Human genes 0.000 claims 1
• 108010012236 Chemokines Proteins 0.000 claims 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
• 240000008415 Lactuca sativa Species 0.000 claims 1
• 235000003228 Lactuca sativa Nutrition 0.000 claims 1
• 241001465754 Metazoa Species 0.000 claims 1
• 244000170916 Paeonia officinalis Species 0.000 claims 1
• 235000006484 Paeonia officinalis Nutrition 0.000 claims 1
• 240000002834 Paulownia tomentosa Species 0.000 claims 1
• 235000010678 Paulownia tomentosa Nutrition 0.000 claims 1
• LOUPRKONTZGTKE-LHHVKLHASA-N Quinidine Natural products C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 claims 1
• LRYXLOJNHFJZDD-UHFFFAOYSA-N [Ag].C1=CC=CC=2C3=CC=CC=C3CC12 Chemical compound [Ag].C1=CC=CC=2C3=CC=CC=C3CC12 LRYXLOJNHFJZDD-UHFFFAOYSA-N 0.000 claims 1
• 230000000844 anti-bacterial effect Effects 0.000 claims 1
• 229910052797 bismuth Inorganic materials 0.000 claims 1
• JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims 1
• LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 claims 1
• 239000002131 composite material Substances 0.000 claims 1
• 230000005611 electricity Effects 0.000 claims 1
• 238000010304 firing Methods 0.000 claims 1
• YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 claims 1
• 150000002386 heptoses Chemical class 0.000 claims 1
• 238000007031 hydroxymethylation reaction Methods 0.000 claims 1
• 150000002500 ions Chemical class 0.000 claims 1
• 238000004898 kneading Methods 0.000 claims 1
• 239000010985 leather Substances 0.000 claims 1
• 229940050176 methyl chloride Drugs 0.000 claims 1
• DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 1
• 238000006386 neutralization reaction Methods 0.000 claims 1
• RLZZZVKAURTHCP-UHFFFAOYSA-N phenanthrene-3,4-diol Chemical compound C1=CC=C2C3=C(O)C(O)=CC=C3C=CC2=C1 RLZZZVKAURTHCP-UHFFFAOYSA-N 0.000 claims 1
• 229960001404 quinidine Drugs 0.000 claims 1
• 230000003252 repetitive effect Effects 0.000 claims 1
• 239000004575 stone Substances 0.000 claims 1
• WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims 1
• 239000010937 tungsten Substances 0.000 claims 1
• 229910052720 vanadium Inorganic materials 0.000 claims 1
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 51
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 45
• 210000004027 cell Anatomy 0.000 description 27
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 23
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